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US 2003/0166932 A1Published application
Amines substituted with a dihydronaphthalenyl, chromenyl, or thiochromenyl group, an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity
OwnerRichard L. Beard, Thong Vu +3inventors
InventorsRichard L. Beard, Thong Vu, Diana F. Colon, Vidyasagar Vuligonda, Roshantha A. Chandraratna
Life of this patent
Estimating the term…
Abstract
Compounds of the formula 1 where the symbols are as defined in the specification, have retinoid agonist, antagonist or negative hormone-like biological activity.
Claims33
A compound of the formula
- 18
- where X is O, S, or C(R)2;
- R is H or alkyl of 1 to 6 carbons;
- R1 is H, alkyl of 1 to 10 carbons, alkenyl of 2 to 6 carbons;
- phenyl-C1-C6 alkyl, or C1-C6-alkylphenyl;
- R2 is H, alkyl of 1 to 6 carbons, F, Cl, Br, I, CF3, fluoro substituted alkyl of 1 to 6 carbons, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R3 is independently alkyl of 1 to 6 carbons, F, Cl, Br, I, CF3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 10 carbons, fluoroalkoxy of 1 to 6 carbons, alkylthio of 1 to 6 carbons;
- benxyloxy, C1-C6 alkyl substituted benzyloxy, halogen substituted benzyloxy, phenyloxy, C1-C6 alkyl substituted phenyloxy, or halogen substituted phenyloxy;
- R4 is independently H, alkyl of 1 to 6 carbons, or F;
- Y is a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said phenyl and heteroaryl groups being optionally substituted with one or two R2 groups;
- m is an integer having the values 0 to 3;
- o is an integer having the values 0 to 4;
- A is (CH2)q where q is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds, and
- B is hydrogen, COOH, COOR8, CONR9R10, —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, —COR7, CR7(OR12)2, CR7OR13O, or tri-lower alkylsilyl, where R7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R8 is phenyl or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons, or a pharmaceutically acceptable salt of said compound.
11 more elements
A compound that has the structure of formula (i), (ii) or (iii)
- 19
- where R is independently H or alkyl of 1 to 6 carbons;
- R1 is H or alkyl of 1 to 10 carbons or alkenyl of 2 to 6 carbons;
- R3 is independently alkyl of 1 to 6 carbons, F, Cl, Br, I, CF3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 10 carbons, fluoroalkoxy of 1 to 6 carbons, alkylthio of 1 to 6 carbons;
- benxyloxy, C1-C6 alkyl substituted benzyloxy, halogen substituted benzyloxy, phenyloxy, C1-C6 alkyl substituted phenyloxy, or halogen substituted phenyloxy;
- R4 is H or alkyl of 1 to 6 carbons;
- A is (CH2)q where q is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds, and
- B is hydrogen, COOH, COOR8, CONR9R10, —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, —COR7, CR7(OR12)2, CR7OR13O, or tri-lower alkylsilyl, where R7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R8 is phenyl or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons, or a pharmaceutically acceptable salt of said compound.
5 more elements
A compound of the formula
- 20
- where R1 is alkyl of 1 to 6 carbons or alkenyl of 2 to 6 carbons;
- R3 is H, alkyl of 1 to 6 carbons, OH, or alkoxy of 1 to 10 carbons, benzyloxy;
- or C1-C6 alkyl substituted benzyloxy;
- R4 is alkyl of 1 to 6 carbons, and
- R8 is H or alkyl of 1 to 6 carbons, or a pharmaceutically acceptable salt of said compound.
3 more elements
A compound of the formula
- 21
- where R1 is alkyl of 1 to 6 carbons or alkenyl of 2 to 6 carbons;
- R3 is H, alkyl of 1 to 6 carbons, OH, or alkoxy of 1 to 10 carbons, or benzyloxy;
- R4 is alkyl of 1 to 6 carbons, and
- R8 is H or alkyl of 1 to 6 carbons, or a pharmaceutically acceptable salt of said compound.
2 more elements
A compound of the formula
- 22
- where R3 is H, or alkyl of 1 to 6 carbons;
- R4 is alkyl of 1 to 6 carbons, and
- R8 is H or alkyl of 1 to 6 carbons, or a pharmaceutically acceptable salt of said compound.
1 more element
Dependencies are inferred from the claim text.